After a three-year hiatus, the franchise was resurrected, this time in Pittsfield, Massachusetts as the Berkshire Black Bears, playing at historic Wahconah Park.

Their first season saw them leading the Northeast League South Division for most of the first half of the season, but the team severely faltered down the stretch and ended up losing the division to the eventual league champion New Jersey Jackals in a one-game playoff at Yale Field.

The bad streak continued, and the Cutters fell to last place in the division in the second half and cost first-year manager Jarvis Brown, a former Minnesota Twins prospect, his job.

In 2005, led by first-year manager Mike Church, the Cutters' fortunes started out badly in the first half with an 18–28 record.

However, in the second half, they had a complete reversal of fortune and won their first half-season division championship, with a 28–18 record, and qualified for the Can-Am League playoffs.

[4] However, the Cutters' luck ran out in the first round of the playoffs, as they were eliminated 3 games to 1 by the eventual league champion Worcester Tornadoes.